One Sunday evening in April 2004, 32-year-old professional gambler Mr Ashley Revell walked into Las Vegas' Plaza Hotel & Casino in a black tuxedo. His aim? To take the $135,300 he'd made the previous month selling everything he owned - including the clothes off his back - and place it on the roulette table in one gigantic, double-or-nothing bet. Pick right between black and red and he'd be twice as rich; wrong, and he'd walk away with nothing. Literally.

Nearly 10 years later, the story, along with the romantic imagery, has entered gambling folklore, but the question of whether Mr Revell won or lost hardly ever gets mentioned. And does it matter? Brooklyn-born actor Mr Michael Kenneth Williams, who performs a stylised retelling of the story in a short film produced by MR PORTER, doesn't seem to think so. And he should know. Before he landed the role of nihilistic antihero and fan favourite Omar Little in The Wire - the part that transformed him into a highly sought-after character actor at the age of 36 - he struggled in obscurity for decades and, like Mr Revell, says there was more than one instance when everything was on the line.

"It felt like my life," he says about the film's script, penned by British writer Ms Sarah Scougal, the first time he read it. "It was so spot-on to my personal journey." (One should point out that things are a lot better today: along with a recurring role in the epic HBO drama Boardwalk Empire, Mr Williams also has appearances in the rebooted Robocop film, and Mr Steve McQueen's Shame follow-up, 12 Years a Slave, which is lined up for next year.)

Speaking from California, where he is currently working on a new blockbuster video game for EA Sports (he can't say which one, just that it's "a big one"), we talked more about what it's like to put it all on the line and how, through thick and thin, style has always played the biggest part in defining Mr Williams' identity.

At 18 I was like, screw it, I'm gonna dress like me. I bought my first pair of penny loafers, and started wearing things like cashmere coats

What interested you in the MR PORTER film?

This question "What is style?" really spoke to me.

So what is style then, for you?

For me it's swagger. It's not about what you're wearing; it's how you wear it. Growing up in Flatbush, my mum made a lot of my clothes for me, and I couldn't afford the fancy things kids were wearing. But as long as I wore what I had with flare, it was style.

Did you try to emulate anyone?

I wasn't big on looking like anybody. I just wanted to fit in. Never blend in, just be yourself whether people accept you or not. It took a while for me to accept that.

Why did you want to blend in?

Until the age of about 17 or 18 I had an identity crisis. I felt like a biracial child because my mum was from the Bahamas and my dad was from the South. My neighbourhood was split between Caribbean and African-American communities, and there was a lot of trouble between the two that I didn't want to get caught up in. So, Tuesday and Wednesday I'd have my beanie hat and red, yellow and green belt, which looked more dread. Then on Thursdays, Fridays and Saturdays I had my Pumas and Adidas, or bucket Kangol, if it didn't get stolen from me, which were more African-American.

What happened for you to finally be OK with dressing how you wanted?

At 18 I was like, screw it, I'm gonna dress like me. I bought my first pair of penny loafers, and started wearing things like cashmere coats. My neighbourhood was pretty conservative, so walking around in a Michael Jackson jacket, penny loafers and Ray-Bans meant I caught a lot of flack.

Yes. I wanted to make sure he looked like a Baltimorean. They dress a certain way in Baltimore. There is a lot of creativity: local dudes make their own T-shirts, and they're happy to wear local Baltimore designers such as We Are One. I didn't want him to look like a Brooklyn guy, where it's all about Fubu and Rocawear.

You hear a lot about Baltimore being a creative place, not just in terms of fashion, but music and clubs too.

Ain't nothing like a Baltimore club. I call Baltimore my second home. After season one [of The Wire] I moved there. It was a vibration I hadn't seen before.

Do you get mobbed when you go back?

It's not the kind of town where people get star struck. If you walk into a club it's going to be on fire if you're there or not. Still, it's what they call a "pig skin" city, so the only time you'll see girls flock to a table is for an athlete.

Do you still have a favourite club?

There is a spot off Charles Street called Eden's Lounge. Ask for a lady named Helen and say Mike sent you. You'll have a great time.

How about in New York?

Two friends of mine, Mark Birnbaum and Eugene Remm, own a couple of clubs in the Meatpacking District, and they've adopted me as family. I'm surprised when they say that, because any given night you can see Jay-Z, Nas or Leonardo DiCaprio in one of their clubs. I met Puff in Catch [one of their restaurants] and right after he put me on a helicopter and told me I was going to Vegas to film a CÃ®roc commercial with him.

I don't play the tables but definitely consider myself a gambler in life. I'm not stupid or reckless, but I didn't get this far by playing it safe

It's funny because the MR PORTER film was shot in one of the oldest members clubs in New York. It sounds as if you've cultivated something similar.

For me their places are like my Cheers. I go there when I want to eat some food, listen to some good music, be among my peers and have a good time. It's priceless. Growing up in Brooklyn I always felt on the outskirts of New York because we were poor. I knew I was in one of the greatest cities in the world, but I never had access to it. Now I'm getting introduced to New York all over again and growing up with it as it grows.

Are you the kind of person to take big risks?

I don't play the tables but definitely consider myself a gambler in life. I'm not stupid or reckless, but I didn't get this far by playing it safe. Before I was cast in Boardwalk Empire I was in South Africa doing a show and had to ask to be let out of my contract, because the character wasn't challenging me and I felt bored. I loved all my co-stars and was having a great time in Cape Town, but I knew deep down inside there was nothing there for me. It was scary because I didn't know what was on the horizon, and it was only later on I was offered the part of Chalky.

If you had to sell all of your possessions, which one item would you keep?

Probably my Bible. If I'm selling everything it probably means my back is up against the wall, and that's a good time for some spirituality.